City Guides: Things to do While Boating in Sleepy Hollow, New York

City Guides: Things to do While Boating in Sleepy Hollow, New York

The town of Sleepy Hollow is well-known for a certain headless horseman (thank you, Washington Irving), a boatload of Halloween events and the beautiful Hudson River Valley. Located north of Yonkers and south of Albany, Sleepy Hollow offers attractions for the whole crew. It sits on the east side of the Hudson River where water-based activities include kayaking, sailing and the nearby Hudson RiverWalk Park at Tarrytown.

In addition to the famous book, Sleepy Hollow has lent its name and historic persona to movies and television, including the Gothic-like 1999 tale starring Johnny Depp and Christina Ricci and a Fox TV series (2013-2017) starring Tom Mison and Nicole Behrie.

If you’re as curious as we are about this quaint little village, keep reading to discover outdoor attractions, historic landmarks and other things to do from a hotel or private boat slip rental in Sleepy Hollow.

Kykuit, the Rockefeller Estate

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Photo: Kykuit, the Rockefeller Estate (Facebook)

Take a step into the early 20th century from a hotel, marina or private boat lift for rent. Kykuit, the Rockefeller Estate, home of the well-known Rockefeller family, sits on 3,400 acres and features a 40-room stone mansion estate with gardens, 20th-century sculptures, art galleries and stunning river valley views. Tour the historic house, which is filled with antique furniture, elegant accessories and opulent window and wall coverings. Historic sites on the property include the 1750 Phillipsburg Manor and a gristmill.   

Rockefeller State Park Preserve

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Photo: Rockefeller State Park Preserve (Facebook)

Walk along wildflower-filled valleys, wide-open pastures and oak, poplar and maple-lined pathways at Rockefeller State Park Preserve. Go fishing, hiking, birdwatching and horseback riding, or check out the historic carriage roads. These wide stone roads are about 16 feet wide and were used at the beginning of the 20th century (Can’t you just picture Ichabod Crane riding down one of them?). There’s a fern garden, a tree peony garden, the 22-acre Swan Lake and the Rockefeller Art Gallery.

Sleepy Hollow Cemetery

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Photo: Flickr/Garrett Zieglar/CC

The historic Sleepy Hollow Cemetery, founded in 1849, is the final resting place of notable names like Andrew Carnegie, Washington Irving, Elizabeth Arden and William Rockefeller. Take a guided tour, visit the 17th-century Old Dutch Reformed Church or walk across the Headless Horseman Bridge, which crosses the Pocantico River.

Don’t miss the Headless Horseman Statue. It’s located between the Old Dutch Church and Philipsburg Manor on Old Broadway. The steel statue is 18 feet tall and one of the most visited attractions in Sleepy Hollow.

Kingsland Point Park

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Photo: Visit Sleepy Hollow (Facebook)

Built in 1926, the 18-acre Kingsland Point Park offers terrific views of the Hudson River. Enjoy outdoor recreation and amenities that include a playground, soccer and lacrosse fields, restrooms and picnic facilities. Take a kayak tour to get out on the river before heading back to private boat dock rentals.

Sleepy Hollow Lighthouse

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Photo: Flickr/Daniel Mennerich/CC

The Sleepy Hollow Lighthouse, built in 1883, sits on the east side of the Hudson River just offshore of Kingsland Point Park. the cast-iron caisson sparkplug lighthouse is also known as the Tarrytown Lighthouse and Kingsland Point Light. It’s accessible via a footbridge and guided tours are available. We think it’s one of the top things to do from a private boat lift rental.

We hope you’ve found some new and interesting spots to visit the next time you’re hanging out at a private boat slip for rent in Sleepy Hollow and the Hudson Valley. Let us know your favorites!

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